Aluminium lithium hydride → HCID 58959983, compound

HRID 916041Notes

Reaction equation

HRID 916041 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][C:11]([OH:29])([C:25]([F:28])([F:27])[F:26])[CH2:12][C:13]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])([CH3:15])[CH3:14])[CH:5]=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[CH2:10][C:11]([OH:29])([CH2:12][C:13]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])([CH3:15])[CH3:14])[C:25]([F:28])([F:27])[F:26]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44435662HCID 44435662, compound

Product 1

HCID 58959983HCID 58959983, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled (0° C.) solution of 30 mg (0.069 mmol) of 3-chloro-4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]benzaldehyde in 1 mL THF was added 4 mg (0.104 mmol) lithium aluminum hydride in one portion. The reaction was warmed to room temperature. The reaction was monitored by TLC, cooled to 0° C., quenched with water, diluted with ethyl acetate, dried over magnesium sulfate, and filtered through diatomaceous earth filter agent. The filtrate was concentrated and chromatographed on silica gel eluting with hexanes-ethyl acetate (97:3 to 8:2) to afford 26.5 mg (88%) of the title compound as an oil.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with water
  3. additiondiluted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through diatomaceous earth
  6. filtrationfilter agent
  7. concentrationThe filtrate was concentrated
  8. customchromatographed on silica gel eluting with hexanes-ethyl acetate (97:3 to 8:2)

Sources & evidence

ORD record
ord-8c49f2203b5949fe8484e39765ab7c9b
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

Loading…